South Orleans MA Real Estate & Homes for Sale

Welcome to 82 Main Street, one of Orleans most extraordinary settings in one of the Cape's most coveted villages. Elegantly restored and rich in tradition and character, this impeccably maintained, gracious 9 room enchanting antique encompasses just under 3000 square feet of living space and offers 5 bedrooms, 2 1/2 baths, formal living and dining rooms, a family room, sitting room, a brand new spectacular cook's kitchen with Omega cabinets, granite countertops and premium appliances and an inviting screened porch and two sundecks to enjoy the starry Cape Cod nights. The flexible floor plan blends the charm of yesteryear with the modern amenities of today and lends itself to both a first or second floor primary bedroom with serene water views of Town Cove. Numerous updates include new heat and AC, hot water heaters, paint in and out, new baths, new roof and many new windows. The charming residence exudes character and timeless style inside and out and features wood floors throughout, 2 fireplaces and one of Orleans most peaceful, tranquil settings. Its abundance of space for both family and friends and proximity to Orleans Village Center just add to this stately homes appeal.

Summer is coming! Welcome to Standish Woods in East Harwich. This coveted association with tennis and pickleball courts as well as over 30 acres of deeded open space is the full package for both relaxation and recreational fun. This custom ranch-style home offers one-floor living which flows from the living room to an upgraded kitchen with cathedral ceilings. There is a great room filled with natural light then directly to the deck & large private backyard. There is a larger primary ensuite which complements two additional bedrooms and a 2nd full bath. A large walk-out basement means possibilities for expansion. This is the perfect spot for year-round or a no-nonsense vacation home set for family and friends. Conveniently located to everything! A stone's throw to the beaches of Pleasant Bay & Cape Cod Bay, drinks at the Wequassett Resort, and swimming at Long Pond, Chatham, and Orleans.

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The lower level also has a guest suite with a full kitchen and living room. The home, close to Lighthouse Beach, comes fully furnished and professionally decorated.

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The home, close to Lighthouse Beach, comes fully furnished and decorated.

Overlooking beautiful Crows Pond, this exquisite property offers a myriad of opportunities with a 6 BR septic and conceptual plans for a 4 BR residence, an existing two bedroom, two bath home that feels like a private sanctuary and exudes a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club, the property offers a multitude of expansion opportunities. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining room are view-filled and adjoin a sunroom with a wood burning fireplace. The kitchen has all the amenities as well as a sitting area that opens to a patio with a fire pit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat.

Overlooking beautiful Crows Pond, this exquisite property has a myriad of opportunities with a six bedroom septic, conceptual building plans for a four bedroom main house and an existing two bedroom, two bath waterfront home that feels like a private sanctuary exuding a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining area are view-filled and adjoin a sunroom with a wood burning fireplace, walls of windows and access to a patio. The kitchen has all the amenities as well as a sitting area that opens to a patio with a firepit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat, but can also provide an exceptional palate to create a custom compound or family property for generations to come.

Welcome to the meticulously maintained 209 Main St. in the heart of East Orleans. The Chefs kitchen is equipped with 6-burner Viking range, custom cabinets, granitecountertops and a spacious island perfect for entertaining. Adjacent to the kitchen is a large welcoming dining area. The Livingroom is highlighted by a wood burning fireplace flanked by custom built-ins. 1st floor ensuite bedroom is complete with custom closets and a beautiful bathroom. Main floor also includes a spacious Den and 2nd bath. Cherry floors with Radiant heat throughout the first level. Two charming bedrooms upstairs with ample closet space. Don't miss the completely rebuilt barn with an open floor plan, kitchenette, laundry, bath and 2nd floor loft. The property is adorned with perennial gardens and was included in the 2023 Hydrangea Festival Tour! Outdoor space: covered porches, deck, terrace, patio, outdoor showers and garden shed. Just minutes to Nauset Beach. Deeded rights to Meeting House Pond.

Welcome to the spectacular 209 Main Street in the heart of East Orleans! Chef's kitchen is a standout, equipped with a 6-burner Viking range, s/s appliances, custom cabinets, honed granite countertops and spacious island perfect for entertaining. Adjacent to kitchen is a large welcoming dining area. Living room is highlighted by a wood burning fireplace flanked by custom built-ins. 1st floor ensuite bedroom is complete with custom closets and beautiful updated bath. Main floor also boasts a spacious den and 2nd full bath. Cherry floors with radiant heat throughout the first level. 2 charming bedrooms upstairs with wide board pine floors and ample closet space. Not to be missed is the completely rebuilt barn with open floor plan, kitchenette, living, dining and office areas, laundry, bath and 2nd floor loft. The property is adorned with multiple perennial gardens, specimen trees and shrubs and was included in the 2023 Hydrangea Festival tour! Outdoor space: fenced private yard, fenced raised bed garden, covered porches, deck, terrace, patio, 2 outdoor showers and a garden shed. Entrance on Cheney road (private Rd)Just minutes to Nauset Beach. Deeded access to Meetinghouse Pond

With a completion date for Spring of 2024, Eastward Companies has a new construction project underway in Orleans. This classic 2,836 sf. home, designed by architect Karen Kempton, features an easy-living floor plan suitable for today's discerning buyer. The open concept design brings the kitchen, dining, and living room together creating an inviting area for all to enjoy. The vaulted ceiling, gas fireplace and custom built-ins add to the allure of this space. A bright and pleasant sun-room with a beamed ceiling and sky light is just off the dining area, providing additional room to spread out and relax. Completing the first floor is a primary en-suite bedroom with tiled shower, double vanity and walk-in closet, pantry, laundry room, powder room, and ample closets. The second floor consists of a landing overlooking the living area, a home office or bonus room, a bedroom with plenty of closet space and a full bath. A third bedroom with its own separate stairway and full bath is over the garage, a private spot ideal for guests. A spacious walkout basement provides opportunity for extra living space. This new home has central air conditioning, gas heat, 1 car garage. Please note there is room for a pool on the property.

Homebuyers, entrepreneurs, and investors- are you looking for a property that has both residential and commercial opportunities located centrally in the East Orleans hamlet? Look no further than 204 Main Street, this iconic property most recently operated as a local doctors' office, offers an expansive range of possibilities for your vision. This property can stay as a commercial venue or be transformed into a one-of-a-kind family home, or a combination home and work oasis. At present, the property features a large, sun-lite commercial space that could be used for a variety of purposes. The property provides a large lot that can be revamped into a beautiful family residence convenient to the village center, beaches, biking, marinas, restaurants, and much more. With this prime location and versatile layout, it's the perfect investment for those who want to live within walking distance of everything, in style, or build a thriving business. Once approved as a private residence, a minimum of 4 bedrooms would be allowed, please call for details.

Homebuyers, entrepreneurs, and investors- are you looking for a property that has both residential and commercial opportunities located centrally in the East Orleans hamlet? Look no further than 204 Main Street, this iconic property most recently operated as a local doctors' office, offers an expansive range of possibilities for your vision. This property can stay as a commercial venue or be transformed into a one-of-a-kind family home, or a combination home and work oasis. At present, the property features a large, sun-lite commercial space that could be used for a variety of purposes. The property provides a large lot that can be revamped into a beautiful family residence convenient to the village center, beaches, biking, marinas, restaurants, and much more. With this prime location and versatile layout, it's the perfect investment for those who want to live within walking distance of everything, in style, or build a thriving business.

Expansive 5 bedroom, 5 bath home convenient to Nauset Beach and town. First floor has a large open living room with cathedral ceilings, formal dining room with butler's pantry, primary en-suite bedroom, plus bedroom #2. There is a second full bath off the oversized kitchen area, as well as first floor laundry room. 3 Season porch with high ceilings overlooks the spacious back yard. Second floor has another living area, as well as 2 more en-suite bathrooms. The second floor also includes bedroom #5 and a bonus space with full bath in the hall. Second set of stairs lead you down to the side patio and back hall. 7 zone high efficiency forced hot water heating system. Outdoor shower to rinse off after the beach. Relax outside on the large stone patio and enjoy the ample yard and outdoor shower.

Updated Contemporary Cape located across from salt water Meeting House Pond. A perfect location for launching your boat or kayak and exploring Pleasant Bay. Nauset Marine is close by for marina services and mooring. This spacious sunlit contemporary cape has approx. 3500 sq.ft.of stunning living space. An updated designer eat-in kitchen with updated appliances. The living room with walls of glass and fireplace opens to a large family/entertainment room which could be converted to a 1st floor Primary bedroom. On the 2nd level is a large Primary bedroom with fireplace and spa bath, as well as 2 guest bedrooms and full bath. Additional 2nd floor large Bonus Room over the garage can be an office, studio or another bedroom. The walk-out lower ground level with large windows and sliders to the back yard is ready to be finished off. Large private yard and room for a pool. It is a bike ride to Nauset Ocean Beach and a short walk to the Village of East Orleans for fine dining and shopping. This

Updated Contemporary Cape located across from salt water Meeting House Pond. A perfect location for launching your boat or kayak and exploring Pleasant Bay. Nauset Marine is close by for marina services and mooring. This spacious sunlit contemporary cape has approx. 3500 sq.ft.of stunning living space. An updated designer eat-in kitchen with updated appliances. The living room with walls of glass and fireplace opens to a large family/entertainment room which could be converted to a 1st floor Primary bedroom. On the 2nd level is a large Primary bedroom with fireplace and spa bath, as well as 2 guest bedrooms and full bath. Additional 2nd floor large Bonus Room over the garage can be an office, studio or another bedroom. The walk-out lower ground level with large windows and sliders to the back yard is ready to be finished off. Large private yard and room for a pool. It is a bike ride to Nauset Ocean Beach and a short walk to the Village of East Orleans for fine dining and shopping. This large custom built home has many updates including a new roof, skylights, & more. Also a great rental property for location and size.

Modern elegance and unparalleled luxury encompass 146 Strong Island Road. Lavishly appointed details from floor to ceiling complement the water views. Wide plank flooring, custom high end cabinetry & built-ins, Thermador appliances, Quartz countertops, exquisite trim detail & coffered ceilings are a few of the details carefully selected to ensure a perfect blend of comfort and sophistication. Expansive open concept floor plan with well apportioned living and bedroom spaces. Each of the three bedrooms are complete with their own spacious en suite bathroom and walk in closets. The cedar shingle siding and roofing, IPE decking, veneered walls & foundation, natural gas fire pit, and heated salt water gunite pool & spa with pebble finish complement the home's contemporary allure. Experience living within one of North Chatham's most coveted neighborhoods, with association beaches on Pleasant Bay & Crows Pond, association dock. New construction sold furnished ready to enjoy this summer!

Modern elegance and unparalleled luxury encompass 146 Strong Island Road. Lavishly appointed details from floor to ceiling complement the water views. Wide plank flooring, custom high end cabinetry & built-ins, Thermador appliances, Quartz countertops, exquisite trim detail & coffered ceilings are a few of the details carefully selected to ensure a perfect blend of comfort and sophistication. Expansive open concept floor plan with well apportioned living and bedroom spaces. Each of the residence's three bedrooms are complete with their own spacious en suite bathroom and walk in closets. The cedar shingle siding and roofing, IPE decking, veneered walls & foundation, natural gas fire pit, and heated salt water gunite pool & spa with pebble finish complement the home's contemporary allure. Experience living within one of North Chatham's most coveted neighborhoods, with private association beaches on Pleasant Bay and Crows Pond, association dock, and ability to join waitlist for a mooring in the association's mooring field on Crow's Pond. New construction homes are few and far between in Chatham so seize your opportunity to capture this stunning turn key furnished triple gambrel.

Discover the charm of Ocean Edge Resort with this meticulously maintained C-style townhouse. The inviting first floor boasts hard surface flooring with a combination of tile & laminate flooring, an impeccably designed kitchen, and a snug corner fireplace for cozy evenings. Upstairs, two generously sized bedrooms await, accompanied by a full bathroom and convenient washer & dryer. Revel in the modern touch of updated windows and sliders, leading to your own private patio retreat with storage shed for your beach gear. Whether you're seeking a year-round residence, an investment opportunity, or a vacation escape, this property is the epitome of versatile coastal living. Offered furnished for move in convenience

Discover 102 Howland Circle in the Ocean Edge Resort & Golf Club with this charming B style townhome. Recent updates include fresh paint throughout, new flooring in the primary bedroom and loft, as well as upgraded appliances including a new dishwasher and stove. You will love the natural sunlight this condo receives! The hardwood floors in the main living areas are a lovely bonus.Nestled within the back of Howland Village in Ocean Edge, this condo offers not just a home but a lifestyle. Find yourself in the beauty of Cape Cod living, with easy access to the famous Brewster Flats beaches, Nickerson State Park and the Cape Cod Rail Trail. Whether you seek a perfect getaway or a permanent entryway into the Cape Cod experience, this townhome is ready for you!

Discover 102 Howland Circle in the Ocean Edge Resort & Golf Club with this charming B style townhome. Recent updates include fresh paint throughout, new flooring in the primary bedroom and loft, as well as upgraded appliances including a new dishwasher and stove. You will love the natural sunlight this condo receives! The hardwood floors in the main living areas are a lovely bonus.Nestled within the back of Howland Village in Ocean Edge, this condo offers not just a home but a lifestyle. Find yourself in the beauty of Cape Cod living, with easy access to the famous Brewster Flats beaches, Nickerson State Park and the Cape Cod Rail Trail. Whether you seek a perfect getaway or a permanent entryway into the Cape Cod experience, this townhome is ready for you!

Discover the charm of Ocean Edge Resort with this meticulously maintained C-style townhouse. The inviting first floor boasts hard surface flooring with a combination of tile & laminate flooring, an impeccably designed kitchen, and a snug corner fireplace for cozy evenings. Upstairs, two generously sized bedrooms await, accompanied by a full bathroom and convenient washer & dryer. Revel in the modern touch of updated windows and sliders, leading to your own private patio retreat with storage shed for your beach gear. Whether you're seeking a year-round residence, an investment opportunity, or a vacation escape, this property is the epitome of versatile coastal living. Offered furnished for move in convenience.

Lowest priced A style Townhouse, motivated seller! Discover spacious and comfortable living in this stunning A style townhouse, the largest of the townhouses in Ocean Edge. Step inside to find a thoughtfully designed open kitchen boasting additional storage and counter space, perfect for culinary enthusiasts and gatherings with loved ones. Stay cozy during the chilly seasons with a brand new gas heater in the inviting living room, a welcoming centerpiece for relaxation. This home has been thoughtfully updated with modern touches, including updated windows and a slider that bathes the interior in natural light while maintaining energy efficiency. Enjoy your own private oasis outdoors with a secluded patio, perfect for al fresco dining or simply unwinding after a long day. The added convenience of a storage shed ensures you have ample space for your outdoor belongings. This townhouse offers the ideal blend of space, functionality, and comfort, making it a superb choice for those seeking an upgraded living experience. Don't miss your opportunity to make this your new home sweet home. Schedule a viewing today and envision the possibilities in this delightful property.

Lowest priced A style Townhouse, motivated seller! Discover spacious and comfortable living in this stunning A style townhouse, the largest of the townhouses in Ocean Edge. Step inside to find a thoughtfully designed open kitchen boasting additional storage and counter space, perfect for culinary enthusiasts and gatherings with loved ones. Stay cozy during the chilly seasons with a brand new gas heater in the inviting living room, a welcoming centerpiece for relaxation. This home has been thoughtfully updated with modern touches, including updated windows and a slider that bathes the interior in natural light while maintaining energy efficiency. Enjoy your own private oasis outdoors with a secluded patio, perfect for al fresco dining or simply unwinding after a long day. The added convenience of a storage shed ensures you have ample space for your outdoor belongings. Don't miss your opportunity to make this your new home sweet home.

Discover the perfect blend of comfort and convenience in this 2 bed, 2 bath condo, ideally situated near bay beaches, the scenic rail trail, and Nickerson State Park. The open floor plan offers flexibility, with a first-floor living option and a private patio featuring a storage shed for beach essentials. Upstairs, a large loft serves as an additional overflow area for guests, along with the second full bath, large bedroom and walk in closet. This sun filled end unit comes furnished, offering a ready-to-enjoy living space. Make this Ocean Edge "A style" townhouse your coastal oasis.

Discover the perfect blend of comfort and convenience in this 2 bed, 2 bath condo, ideally situated near bay beaches, the scenic rail trail, and Nickerson State Park. The open floor plan offers flexibility, with a first-floor living option and a private patio featuring a storage shed for beach essentials. Upstairs, a large loft serves as an additional overflow area for guests, along with the second full bath, large bedroom and walk in closet. This sun filled end unit comes furnished, offering a ready-to-enjoy living space. Make this Ocean Edge townhouse your coastal oasis.

NEW Construction home, nestled in the heart of Harwich, a true oasis for any family. This masterfully designed home was completed in 2024 and features 4-bedrooms, 3-bathrooms and offers a peaceful sanctuary of comfort and tranquility. A retreat from the hustle and bustle of city life, a haven for the family. The spacious great room extends into the dining room, with amazing views of the semi-private Great Pond through the enormous bi-folding glass doors. Be one of the handful of homes that has direct access to the water, providing a wonderful opportunity for activities such as fishing, boating, or simply enjoying the natural beauty of the surroundings and what nature has to offer. This home truly serves as a home away from home. Its location, features, and the warmth it offers, makes it the perfect choice for a peaceful retreat to spend your summers, a weekend getaway, or a place to create lifelong memories. (Furniture, TV's and Network equipment are negotiable)